01931nas a2200325   4500008004100000022001400041245006800055210006700123260007700190300001400267490000700281520089600288653001601184653001301200653002101213653002101234653002001255100001701275700001701292700001801309700001801327700002401345700002601369700002601395700001701421700002301438700001801461700002401479856010201503       2015                        eng d  a0947-653900aTotal and semi-syntheses of antimicrobial thuggacin derivatives0 aTotal and semisyntheses of antimicrobial thuggacin derivatives  aBOSCHSTRASSE 12, D-69469 WEINHEIM, GERMANYbWILEY-V C H VERLAG GMBHcMAR  a4272-42840 v213 a<p>The total and semi-synthesis of 13 new macrolactones derived from thuggacin, which is a secondary metabolite from the myxobacterium Sorangium cellulosum, are reported. The thuggacins have attracted much attention due to their strong antibacterial activity, particularly towards Mycobacterium tuberculosis. This study focuses on 1) thuggacin derivatives that cannot equilibrate by transacylation between the three natural thuggacins A-C, 2) the roles of the thiazole ring, and 3) the hexyl side chain at C2. Semi-synthetic O-methylation at C17 suppressed the transacylations without a substantial loss of antibacterial activity. Exchanging the C17-C25 side chain for simplified hydrophobic chains led to complete loss of antibacterial activity. Exchange of the thiazole by an oxazole ring or removal of the hexyl side chain at C2 had no substantial effect on the biological properties.</p>10aantibiotics10alactones10aNatural products10asynthesis design10aTotal synthesis1 aFranke, Jana1 aBock, Martin1 aDehn, Richard1 aFohrer, Joerg1 aMhaske, Santosh, B.1 aMigliorini, Antonella1 aKanakis, Argyrios, A.1 aJansen, Rolf1 aHerrmann, Jennifer1 aMueller, Rolf1 aKirschning, Andreas  uhttps://library.ncl.res.in/content/total-and-semi-syntheses-antimicrobial-thuggacin-derivatives-0